5-methoxycarbonylethyl-2'-deoxyuridine | 96203-39-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5-methoxycarbonylethyl-2'-deoxyuridine
• 英文别名: methyl 3-[1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4-dioxopyrimidin-5-yl]propanoate
• CAS: 96203-39-3
• 化学式: C₁₃H₁₈N₂O₇
• 分子量: 314.295
• InChiKey: YKCGPJXDHZCMKU-IVZWLZJFSA-N

物化性质

• 密度：
  1.422±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-methoxycarbonylethyl-2'-deoxyuridine 在 吡啶 、 二异丙基铵盐四氮唑 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 3’-O-(2-cyanoethyl-N,N-diisopropylaminophosphinoxy)-5’-O-(4,4’-dimethoxytrityl)-5-[2-(trifluoroacetylamino)ethylaminocarbonylethyl]-2’-deoxyuridine
  参考文献：
  名称：

  Studies on the Two Thymine Residues in the Catalytic Core of 10-23 DNAzyme: The Impact on the Catalysis of Their 5-Substituted Functional Groups

  摘要：

  在 10-23 DNA 酶的 15 个聚合物催化核心中，每个残基对催化构象的贡献各不相同。在这里，非常保守的 T4 和最不保守的 T8 在其 5 位上被修饰为具有氢键能力的羟基、咪唑基和氨基。这些外部功能基团在催化核心内诱导了新的相互作用，从而对 10-23 DNA 酶的催化活性产生了消极和积极的影响，不同的连接方式可用于调节功能基团的作用。在核碱基水平上，T4 和 T8 的保守性可以得到认可，但在官能团水平上，T4 并不完全保守。可以对它们的 5-甲基基团进行修饰，以提高 DNA 酶的性能。

  DOI：

  10.3390/molecules22071011
• 作为产物：
  描述：

  碘苷 在 palladium on activated charcoal palladium diacetate 、 氢气 、 三乙胺 、 三苯基膦 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 25.0 ℃ 、310.27 kPa 条件下， 反应 36.0h， 生成 5-methoxycarbonylethyl-2'-deoxyuridine
  参考文献：
  名称：

  Synthesis of 5-Tethered Carborane-Containing Pyrimidine Nucleosides as Potential Agents for DNA Incorporation

  摘要：

  Several 5-substituted-2'-deoxyuridines have been prepared in which the carborane moiety is attached at the terminus of a flexible hydrocarbon chain containing an ester linkage. These boron moieties as the B-10 enriched compounds have potentiality for use in the treatment of cancer by means of boron neutron capture therapy. A convenient synthetic route, in high yield, has been developed for the preparation of these 5-tethered carborane-containing pyrimidine nucleosides.

  DOI：

  10.1080/15257779408010680

文献信息

• Synthesis and characterization of DNA oligomers and duplexes containing covalently attached molecular labels: comparison of biotin, fluorescein, and pyrene labels by thermodynamic and optical spectroscopic measurements
  作者：Joshua Telser、Kenneth A. Cruickshank、Larry E. Morrison、Thomas L. Netzel

  DOI：10.1021/ja00200a011

  日期：1989.8

  Synthese de nucleotides modifies, de la cytidine et de l'uridine, permettant la liaison avec des composes fluorescents tel que la biotine, le pyrenebutyrate-1, la fluorescesine, afin de rendre fluorescent des oligonucleotides

  Synthese de nucleotides modates, de la cytidine et de l'uridine, permettant la liaison avec des composesfluores tel que la biotine, le pyrenebutyrate-1, la fluorescesine, afin de rendrefluorescence des oligonucleotides
• 核苷类化合物或其盐、核酸及其应用
  申请人：中国人民解放军军事医学科学院毒物药物研 究所

  公开号：CN107236011B

  公开（公告）日：2020-11-27

  本发明属于生物医药领域，涉及一种核苷类化合物或其盐、核酸及其应用。具体地，本发明涉及式Ⅰ所示的核苷类化合物或其盐；在此基础上，本发明还涉及核酸。本发明的核酸可用作催化血管内皮生长因子受体2的mRNA裂解的脱氧核酶或者用作与人促红细胞生成素有亲和作用的适配体。
• 5-(Haloalkyl)-2'-deoxyuridines: a novel type of potent antiviral nucleoside analog
  作者：Herfried Griengl、Michael Bodenteich、Walter Hayden、Erich Wanek、Wolfgang Streicher、Peter Stuetz、Helmut Bachmayer、Ismail Ghazzouli、Brigitte Rosenwirth

  DOI：10.1021/jm00149a024

  日期：1985.11

  Syntheses of 5-(2-haloethyl)-2'-deoxyuridines, 5-(3-chloropropyl)-2'-deoxyuridines, and 5-(2-chloroethyl)-2'-deoxycytidine are described. The antiviral activities of these compounds were determined in cell culture against herpes simplex virus types 1 and 2. All compounds were shown to possess significant and selective antiviral activity. The most potent derivative, 5-(2-chloroethyl)-2'-deoxyuridine

  描述了5-（2-卤乙基）-2'-脱氧尿苷，5-（3-氯丙基）-2'-脱氧尿苷和5-（2-氯乙基）-2'-脱氧胞苷的合成。在细胞培养物中确定了这些化合物对1型和2型单纯疱疹病毒的抗病毒活性。所有化合物均显示出显着的选择性抗病毒活性。最有效的衍生物5-（2-氯乙基）-2'-脱氧尿苷（CEDU）在浓度低于0.1微克/毫升时抑制HSV-1。仅在浓度高于100微克/ mL时，它对细胞增殖才产生可测量的抑制作用。体内CEDU腹膜内和口服给予的浓度低于每天5 mg / kg的小鼠，可降低HSV-1感染小鼠的死亡率。从而，
• Hassan, Mohamed E., Recueil des Travaux Chimiques des Pays-Bas, 1986, vol. 105, # 1, p. 30 - 32
  作者：Hassan, Mohamed E.

  DOI：——

  日期：——
• Synthesis and Evaluation of “AZT-HEPT”, “AZT-Pyridinone”, and “ddC-HEPT” Conjugates as Inhibitors of HIV Reverse Transcriptase
  作者：Renée Pontikis、Valérie Dollé、Jean Guillaumel、Elsa Dechaux、Reine Note、Chi Hung Nguyen、Michel Legraverend、Emile Bisagni、Anne-Marie Aubertin、David S. Grierson、Claude Monneret

  DOI：10.1021/jm991125l

  日期：2000.5.1

  To test the concept that HIV reverse transcriptase could be effectively inhibited by "mixed site inhibitors", a series of seven conjugates containing both a nucleoside analogue component(AZT 1, ddC 2) and a nonnucleoside type inhibitor (HEPT analogue 12, pyridinone 27) were synthesized and evaluated for their ability to block HIV replication. The (N-3 and C-5)AZT-HEPT conjugates 15, 22, and 23 displayed 2-5 mu M anti-HIV activity, but they had no effect on the replication of HIV-2 or the HIV-1 strain with the Y181C mutation. The (C-5)AZT-pyridinone conjugates 34-37 were found to be inactive. In marked contrast, the ddC-HEPT molecule 26 displayed the same potency (EC50 = 0.45 mu M) against HTV-1 (wild type and the Y181C nevirapine-resistant strain) and HIV-2 in cell culture. No synergistic effect was-observed for these bis-substrate inhibitors, suggesting that the two individual inhibitor components in these molecules do not bind simultaneously in their respective sites. Interestingly, however, the results indicate that the AZT-HEPT conjugates and the ddC-HEPT derivative 26 inhibit reverse transcriptase (RT) in an opposite manner. One explanation for this difference is that the former compounds interact preferentially with the hydrophobic pocket in RT, whereas 26 (after supposed triphosphorylation) inhibits RT through binding in the catalytic site.